The Art of Sailing

Best way to boat. Maybe you can get with Below Deck Sailing. Actually contacting the Moorings would be a good place to start.

BVI's is the best place for that. Only 5-10 NM's to each island!!!!

Yes BVI is very accessible. But a bit touristy. If we were to charter 35-40m sailboat I think Caribbean would be better.

Bare boat? How large? Cat or Mono? Anchorage hopping or sailing overnight? It seems so prudent to charter rather than own, well, having a day sailing vessel is how I prefer to deal with the sailing bug. I would not take the time or effort to sail up and down a coast, I would rather charter at the destination and anchor hop and chill.
I heart sailing. My wife just bought a Hobie Wave. Most fun we had all summer.

You might also look into Windjammer cruises for a more hands on experience.

With the whole family we would want 100-120'. Service is king. I just think it would be perhaps an even more relaxing charter being able to see all the work that goes into a large sailing yacht.

I think that with most large yacht charters one goal is for you not to see the work involved.

No, no, no. I want to see that perfect martini, an amazing meal, perfect service. And seeing skills folks get a large sailboat up to 15 kts would be a blast.

Perfection.

Although I can't claim to ever have participated at this level, I do consider this highest level version of the "sport" part of my heritage, and I spent a lot of hours being cold and wet chasing and being chased at the lower levels...........

Fun to watch....impressed seeing them pull on three strand lines bare handed. No hi-tech sailing gloves, deck shoes, or carbon fiber hulls for those sailors.